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Port: Philipsburg, St. Maarten×
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46% OFF
MSC Meraviglia
MSC Cruises
Jan 16, 2027 - Jan 30, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Puerto Plata, Dominican Republic • Miami • Nassau • Ocean Cay • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,175pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Dec 17, 2026 - Dec 27, 2026 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,179pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Crown Princess
Princess Cruises
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,011pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Star Princess
Princess Cruises
Dec 2, 2028 - Dec 16, 2028 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$2,044pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

49% OFF
MSC World Asia
MSC Cruises
Feb 22, 2028 - Mar 7, 2028 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Bridgetown, Barbados
Average Starting Price
$2,359pp
Jim's Onboard Credit
40% OFF
MSC Opera
MSC Cruises
Aug 6, 2027 - Aug 13, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique
Average Starting Price
$1,337pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Dec 6, 2027 - Dec 27, 2027 (21 Nights)
Lisbon, Portugal • Funchal, Portugal • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$6,298pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$949pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 13, 2028 - Feb 27, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,483pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 10, 2028 - Dec 20, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$3,799pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 27, 2028 - Mar 5, 2028 (7 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$835pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

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